Crossdresser Proper Lady Stories

104,639 results
Orientation
Length
Source
Infinite Scroll

My First Time Dressing Ch. 01

by ChrissyCD on Sep 16, 2017
Transsexuals & Crossdressers

This is the first of hopefully many stories to come. This one may be a bit boring and lacking the hardcore fucking and sucking so many of you are used to. I feel the need to tell it because it will give some background to the rest of my stories. For the most part I will send them in chronologically from my younger days to present day as a undercover crossdre...

Jack's First Time

by bi_cpl_with_crossdresser on Jul 13, 2020
Transgender & Crossdressers

There were no secrets between Jack and Marcy, hell when you have been married to the same person for almost 24 years and together for even longer there was no need. Marcy had professed to Jack well before they were even a couple that she was bi and soon after they were dating Jack confessed he was a Crossdresser, a few years later he also said he thought h...

A Wife A Little To Understanding

by felicia_rene on Oct 12, 2020
Transgender & Crossdressers

Present day: We arrived at the 'Sissy Salon' which was a covert sex club for downlow gay wealthy men and lesbians. As his agent and pimp I collected all his performance fees. I walked into the 'Sissy Salon' to make sure that everything was in place so my sissy husband could perform. Then I went to his dressing room to make sure everything I requested for me...

Becoming Jessica Pt. 03

by Lovely_Jessica on Sep 25, 2017
Transsexuals & Crossdressers

To recap: I came out to my wife Emma yesterday that I was a crossdresser and was considering transitioning into a woman. After some initial grief she became supportive and helped me fully dress as a woman for the first time. We even went on an impromptu 'girls night out' at a piano bar in a local hotel/resort in suburban Chicago where I met a man named Drake...

Kerri's Costume Party

by CorsetCutie69 on Sep 12, 2017
Transsexuals & Crossdressers

Let me start by saying that I have been a closet crossdresser since I was quite young. I have kept it a close secret for over 20 years now. I consider myself to be a semi-normal straight heterosexual married male with a liking for the softer side. I let my wife discover my secret about 3 years ago, after over 7 years of marriage. She was very supportive of m...

A New City Ch. 01

by Heartbloodblack on Sep 16, 2017
Transsexuals & Crossdressers

I stepped on to bus 55, paid my fair, and walked to the first empty seat on the bus. Smoothing my white and pink floral blouse, then my matching knee length skirt. I looked around the bus, nobody interesting. The bus was mostly the same as any other bus someone might ride to work or to school. It had a set of yellow rails with blue hand straps that you mig...

Her Surprise

by dickital on Sep 16, 2017
Sci-Fi & Fantasy

The bell jingles as the door opens, the toys outside were enticing, but the store inside opens your eyes. Though it is a small shop, it manages to cater for as many different fetishes as you could imagine. One wall is dedicated for the ass, dildos, inflateable, lockable, ejaculating, big ones, small ones, tentacle which move on their own. Two walls are dedic...

Finally a Princess Pt. 02

by fireandlace0533 on Sep 14, 2020
Transgender & Crossdressers

Part two of a crossdresser who loves Disney who has come out to his wife while on a Disney Cruise. New experiences and adventures are ahead. Finally a Princess (Part Two) I woke the next morning around six thirty which was a little late for me. I laid in bed and thought about what had happened yesterday. I had actually spent time in front of my wife Sarah...

My Life as a Crossdresser Ch. 01

by asian_CD on Sep 16, 2017
Transsexuals & Crossdressers

Hi, This is my first ever attempt at writing a story so I would appreciate constructive feed back. Also, this is just mainly set up and background info with only a masturbation scene. Some of the following events are true and did happen to me. ********************************** It has been five months since I turned 18 and thankfully, high school was in...

Drones 2

by Nils Huim on Nov 26, 2017
Transsexuals & Crossdressers

My first experience with drones, outside of the military that is, was one weekday when I was standing behind a small copse (water-starved trees, shrubs) in the netherlands of a public park near my home. Off to my right a dried-up lake bed; behind me, at some distance, the foresty park proper with its interlaced hiking trails. I was naked except for women's p...